I goofed, and during the filling out of my TurboTax for my rental properties (2018 TY), I realized I forgot about looking into and sending this one contractor a 1099-MISC. Now that it's late, it appears that I'll be fined up to $100 (I forget where I read that...possibly in TurboTax or on IRS site).

I have a couple of questions about this. He did about $1100 of work in one unit and $300 in a second unit. Am I supposed to combine that into a single 1099-MISC since they're different tax forms for me that I file for each unit? Or, do I not need to file the amount for the second unit since it falls under the $600 threshold? I'm guessing I file a single 1099-MISC for $1400 for him.

Now that I'm late, I'm scrambling to figure out how do I get the 1099-MISC form to fill out for him. I found an IRS site that I ordered the form (also one for 2019, just in case) but it will take up to 10 days! Is there any other way to get this form faster? I really feel bad that I'm submitting this form late for him, but I already gave him a heads up that I need to report it.

You are DOOMED! ABANDON ALL HOPE, YOU DIDN'T FILE THE FORM!

Since I do all my own taxes, I guess I'm the accountant! We're not incorporated.

I realize that the IRS isn't out to gouge me, but I'll still be fined for being dumb. I feel bad that I'm filing late for our contractor who I really like.

I'm quite sure you would send the 1099 in the amount of $1400 for all the work he did for the year.

When hiring a freelance worker, handyman or sole proprietor, then the IRS requires you to fill out a 1099 form. This person is not your employee just an occasional worker you've paid $600 or more during a calendar year.

If that person refuses to provide you will this Tax ID or Social Security Number, then to protect yourself, you should do payroll deductions covering the mandatory taxes -- then report them quarterly to the IRS.

If the worker is from a company that employs several people and your payment is to the "known" company (not directly to the employee), then you NOT required to fill out the 1099 form.

Consult with your accountant.

You won't be fined for being dumb. Just mail it in ASAP.

The only 1099 issue I had was with the landscaper that put in an underground sprinkler system at our apartments. I mailed his 1099 by Jan 31st. Three years later I get a form letter from the IRS. Mr. Landscaper had not reported this income, and I had to do a 20% withholding on any future fees we paid him. Since we had already had our own billing issues with this company, we had moved on to another landscaper. I certainly was not going to go through the work of submitting withholding on this jerk.

My accountant just asked me this and I file as an LLC :Did you send Forms 1099-MISC to all un-incorporated individuals and businesses to whom you paid $600 or more? There is a question on the tax forms that ask this now.

Lucy: To answer your question: Yes, you are to ask everyone that you paid $600 or more to what their status is. You "ask" this by having them fill out a W-9.

- John...

And, if we're being picky, you're supposed to have them do the W-9 BEFORE you pay them -- because if they refuse, then you're supposed to start withholding from their pay.

Everyone does it the opposite way, of course, but that's what you're technically "supposed" to do. :)

- John...

I have been using eagleviewfiling dot c o m

They are great for the 2-4 1099's that I need to send out each year. I think it cost $4.50 per 1099. For that they mail the 1099 and then efile with the irs.